Ammonia → Ethyl 2-(4-Bromo-2-chlorophenyl)acetate

Participants

Reaction Steps

(4-Bromo-2-chlorophenyl)-acetic acid (18, 44.03 g, 0.18 mol) was dissolved in ethanol (440 mL) and thionyl chloride (44.0 mL, 0.61 mol) was added dropwise. The mixture was refluxed for 1 h, and evaporated. The residue was taken up in toluene and evaporated (2×100 mL). The crude oily product was dissolved in dichloromethane (300 mL) and washed with water (2×100 mL), dried over sodium sulfate, filtered and evaporated. The residue was dried in high vacuum (0.2 mmHg) at room temperature, solidifying to a light yellow low melting crystalline solid (45.5 g, 0.16 mol, 93%) ESMS m/z 294 [M+H+NH3]+; 1H NMR (300 MHz, CDCl3): δ 7.55 (d, J=2 Hz, 1H), 7.37 (dd, J=8, 2 Hz, 1H), 7.16 (d, J=8 Hz, 1H), 4.18 (q, J=7 Hz, 2H), 3.71 (s, 2H), 1.26 (t, J=7 Hz, 3H).

Provenance & Evidence